(1E,3E)-1,4-Dinitro-1,3-butadiene—Synthesis, Spectral Characteristics and Computational Study Based on MEDT, ADME and PASS Simulation

Molecules, Journal Year: 2024, Volume and Issue: 29(2), P. 542 - 542

Published: Jan. 22, 2024

The chemistry of conjugated nitrodienes is becoming increasingly popular. These molecules are successfully applied in cycloaddition to synthesize six-membered rings Diels-Alder reactions. Nitrodienes can be also obtain bis-compounds [3+2] cycloaddition. Moreover, the presence a nitro group structure provides possibility further modification products. simplest symmetrical representative (1E,3E)-1,4-dinitro-1,3-butadiene. Although first mentions compound date back early 1950s, has not yet been examined thoroughly enough. Therefore, this article, comprehensive study (1E,3E)-1,4-dinitro-1,3-butadiene described. For purpose, an experimental including synthesis process as well evaluation spectral characteristics conducted. So better understand properties compound, computational reactivity indices based on MEDT and assessment pharmacokinetics biological activity according ADME PASS methodologies have made. On basis, some future application trends proposed.

Language: Английский

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Unexpected Course of Reaction Between (1E,3E)-1,4-Dinitro-1,3-butadiene and N-methyl Azomethine Ylide—A Comprehensive Experimental and Quantum-Chemical Study

Molecules, Journal Year: 2024, Volume and Issue: 29(21), P. 5066 - 5066

Published: Oct. 26, 2024

In recent times, interest in the chemistry of conjugated nitrodienes is still significantly increasing. particular, application these compounds as building blocks to obtain heterocycles a popular object research. Therefore, continuation our research devoted topic nitrodienes, experimental and quantum-chemical studies cycloaddition reaction between (1E,3E)-1,4-dinitro-1,3-butadiene N-methyl azomethine ylide have been investigated. The computational results present that tested realized through pdr-type polar mechanism. turn, study shows course this cycloaddition, only one product form 1-methyl-3-(trans-2-nitrovinyl)-Δ3-pyrroline created. constitution compound has confirmed via spectroscopic methods. Finally, ADME analysis indicated synthesized Δ3-pyrroline exhibits biological potential, it good drug candidate according Lipinski, Veber Egan rules. Nevertheless, PASS simulation showed weak antimicrobial, inhibitory antagonist properties. Preliminary silico although obtained not for drug, presence nitrovinyl moiety its structure indicates an initial basis further modifications.

Language: Английский

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Recent Advancement in the Conversion of 1,2,3‐Benzotriazin‐4(3H)‐One to Other Heterocyclic Systems and Their Applications: A Concise Review

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(5)

Published: Feb. 1, 2025

Abstract The nitrogen containing 1,2,3‐benzotriazin‐4(3 H )‐one is structurally worthwhile system for its notable applications in the synthesis of N─ , O ─ and S─ heterocycles bears pivotal significant usage pharmaceutical industrial chemicals. Today most common items like dyes, cosmetics, sanitizers, insecticides plastics are based on heterocyclic moieties. Different starting materials used industrially formation diverse but a valuable structure to prepare numerous products. These conversions radiation or metal‐catalyzed denitrogenation annulation type reactions provide easy, one‐step atom‐economical route. vast significance their cheap make this subject interesting scientific researchers industrialists. This mini review summarizes recent developments transformation ring various other structures phenanthridinones, isoquinolones, coumarin‐1‐imines, benzamides, pyrroloquinazolinones, indolin‐1‐ones, 1,2‐benzisoselenazol‐3(2 )‐ones benzofuranones. Some emerging drugs ebselen, losartan, irbesartan, luotonin A, deoxyvasicinone mackinazolinone have been successfully synthesized from differently substituted benzotriazinones.

Language: Английский

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Improving the Optical and Quantum-Electronic Properties of Pyromellitic Diimide by Thionation: A DFT Study with Promising Applications in Molecular Wires

Chemistry Africa, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 20, 2025

Language: Английский

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Spectroscopic and Nonlinear Optical Insights of Picolinaldehyde‐Based Materials: Experimental and DFT Approach

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(12)

Published: March 1, 2025

Abstract Herein, a series of picolinaldehyde‐based materials ( DMeP‐TFMP ) were synthesized, via the decarboxylative Suzuki coupling reaction using readily accessible 2‐formyl‐6‐pyridinoic acid, to investigate their nonlinear optical (NLO) properties. Various spectroscopic techniques like UV–vis, FT‐IR, ¹H‐NMR, and ¹ 3 C‐NMR employed elucidate molecular structures synthesized chromophores. Further, density functional theory (DFT) time dependent (TD‐DFT) calculations at M06/6‐311G (d,p) level conducted assess frontier orbitals (FMOs), absorption properties, insights. The DMeP displayed minimal band gap (4.390 eV among studied compounds with highest bathochromic shift (340.476 nm). states (DOS) transition matrix (TDM) analyses validated charge transitions from valance conduction band. All exhibited enhanced exciton dissociation rates because low binding energy values E b = 0.525 0.572 ). Furthermore, electron‐hole analysis revealed distribution electron hole densities across different atoms in compounds, indicating significant creation specific atomic sites. notable linear polarizability that is, (⟨α⟩ 2.59 × 10⁻ 2 ‐3.62 esu ), first hyperpolarizability β tot 2.87 ⁰−16.4 ⁰ second γ 1.93 ⁵‐8.44 ⁵ highlighting potential as efficient for advanced NLO applications.

Language: Английский

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Regioselective Synthesis of 5‐(1,2,3‐Triazol‐1‐yl)isoxazoles by Cyclization of 5‐Azidoisoxazoles with Active Methylene Compounds

Asian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

Abstract A facile metal‐free approach to 5‐(1,2,3‐triazol‐1‐yl)isoxazoles bearing a variety of functional groups in both heterocyles has been developed. cyclization 3‐EWG‐5‐azidoisoxazoles with compounds possessing active methylene group proceeds smoothly under mild conditions the presence triethylamine or Cs 2 CO 3 alcohols DMF affording fused hybrid triazole‐isoxazole high yields up 98%. Some mechanistic aspects reaction are discussed.

Language: Английский

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Exploring the nonlinear optical properties of fluorinated aniline derivatives: A computational and experimental study

Computational and Theoretical Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 115224 - 115224

Published: April 1, 2025

Language: Английский

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DFT and TD-DFT/CPCM analysis and pharmacokinetic evaluation of 6-fluoro-4-hydroxy-2-methylquinoline: spectroscopic, HOMO-LUMO, MEP, NLO, NBO, and docking insights with human serum albumin

International Journal of Modelling and Simulation, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 16

Published: April 28, 2025

Language: Английский

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Computational Approach for Molecular Design of Small Organic Molecules with High Hole Mobilities in Amorphous Phase Using Random Forest Technique and Computer Simulation Method

Bulletin of the Chemical Society of Japan, Journal Year: 2023, Volume and Issue: 96(10), P. 1099 - 1107

Published: Aug. 24, 2023

Abstract A molecular design system of small organic molecules was developed to realize high hole mobility in the amorphous phase by using random forest (RF) technique and a computer simulation method. Since there no accessible datasets mobilities phase, we have constructed experimental for 321 with calculated MO energies utilize machine learning techniques procedures. RF applied datasets. The optimized exhibited correlation coefficients 0.885 0.764 training testing datasets, respectively. modified ChemTS use adapted mobilities. successive conduction (SC) model that uses ab initio orbital (MO) calculations Marcus theory ensure predicted generated were verified (the order 10−2 cm2/Vs) owing highest transfer integral lowest reorganization energy theoretical model. programs used this work publicly released on GitHub.

Language: Английский

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Excitons in organic materials: revisiting old concepts with new insights

Electronic Structure, Journal Year: 2023, Volume and Issue: 5(3), P. 033003 - 033003

Published: Aug. 22, 2023

Abstract The development of advanced experimental and theoretical methods for the characterization excitations in materials enables revisiting established concepts that are sometimes misleadingly transferred from one field to another without necessary disclaimers. This is precisely situation occurs excitons organic materials: different states matter peculiarities related their structural arrangements environment may substantially alter nature photo-induced excited compared inorganic semiconductors which concept an exciton was originally developed. Adopting examples tetracene perfluorotetracene, this review, we analyze isolated compounds solution, crystalline materials, melt. Using single crystals or films with large domains polarization-resolved optical absorption measurements, thus determination energy polarization excitons. These experiments complemented by state-of-the-art first-principles calculations based on density-functional theory many-body perturbation theory. employed methodologies offer unprecedented insight into response systems, allowing us clarify single-particle character molecules collective electron–hole pairs aggregated phases. Our results reveal turning point between these two scenarios quantum-mechanical interactions molecules: when wave-function distributions Coulomb among them explicitly described adopted scheme, excitonic transitions can be captured. Semi-classical models accounting only electrostatic couplings photo-activated unable reproduce effects. outcomes work a deeper understanding both perspectives.

Language: Английский

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